Design and synthesis of an inositol phosphate analog based on computational docking studies

Zhenghong Peng; David Maxwell; Duoli Sun; Yunming Ying; Paul T. Schuber; Basvoju A. Bhanu Prasad; Juri Gelovani; Wai Kwan Alfred Yung; William G. Bornmann

doi:10.1016/j.tet.2013.11.092

Design and synthesis of an inositol phosphate analog based on computational docking studies

Zhenghong Peng, David Maxwell, Duoli Sun, Yunming Ying, Paul T. Schuber, Basvoju A. Bhanu Prasad, Juri Gelovani, Wai Kwan Alfred Yung, William G. Bornmann

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

A virtual library of 54 inositol analog mimics of In(1,4,5)P₃ has been docked, scored, and ranked within the binding site of human inositol 1,4,5-trisphosphate 3-kinase A (IP₃-3KA). Chemical synthesis of the best scoring structure that also met distance criteria for 3′-OH to-P in phosphate has been attempted along with the synthesis of (1S,2R,3S,4S)-3-fluoro- 2,4-dihydroxycyclohexanecarboxylic acid as an inositol analog, useful for non-invasive visualization and quantitation of IP₃-3KA enzymatic activity.

Original language	English (US)
Pages (from-to)	984-990
Number of pages	7
Journal	Tetrahedron
Volume	70
Issue number	4
DOIs	https://doi.org/10.1016/j.tet.2013.11.092
State	Published - Jan 28 2014

Keywords

(+)-Cyclophellitol
F-FDMCI- 3′-phosphate
IP-3K
Inositol
Ins(1,4,5)P

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2013.11.092

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title = "Design and synthesis of an inositol phosphate analog based on computational docking studies",

abstract = "A virtual library of 54 inositol analog mimics of In(1,4,5)P3 has been docked, scored, and ranked within the binding site of human inositol 1,4,5-trisphosphate 3-kinase A (IP3-3KA). Chemical synthesis of the best scoring structure that also met distance criteria for 3′-OH to-P in phosphate has been attempted along with the synthesis of (1S,2R,3S,4S)-3-fluoro- 2,4-dihydroxycyclohexanecarboxylic acid as an inositol analog, useful for non-invasive visualization and quantitation of IP3-3KA enzymatic activity.",

keywords = "(+)-Cyclophellitol, F-FDMCI- 3′-phosphate, IP-3K, Inositol, Ins(1,4,5)P",

author = "Zhenghong Peng and David Maxwell and Duoli Sun and Yunming Ying and Schuber, {Paul T.} and {Bhanu Prasad}, {Basvoju A.} and Juri Gelovani and {Alfred Yung}, {Wai Kwan} and Bornmann, {William G.}",

year = "2014",

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doi = "10.1016/j.tet.2013.11.092",

language = "English (US)",

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journal = "Tetrahedron",

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T1 - Design and synthesis of an inositol phosphate analog based on computational docking studies

AU - Peng, Zhenghong

AU - Maxwell, David

AU - Sun, Duoli

AU - Ying, Yunming

AU - Schuber, Paul T.

AU - Bhanu Prasad, Basvoju A.

AU - Gelovani, Juri

AU - Alfred Yung, Wai Kwan

AU - Bornmann, William G.

PY - 2014/1/28

Y1 - 2014/1/28

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AB - A virtual library of 54 inositol analog mimics of In(1,4,5)P3 has been docked, scored, and ranked within the binding site of human inositol 1,4,5-trisphosphate 3-kinase A (IP3-3KA). Chemical synthesis of the best scoring structure that also met distance criteria for 3′-OH to-P in phosphate has been attempted along with the synthesis of (1S,2R,3S,4S)-3-fluoro- 2,4-dihydroxycyclohexanecarboxylic acid as an inositol analog, useful for non-invasive visualization and quantitation of IP3-3KA enzymatic activity.

KW - (+)-Cyclophellitol

KW - F-FDMCI- 3′-phosphate

KW - IP-3K

KW - Inositol

KW - Ins(1,4,5)P

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DO - 10.1016/j.tet.2013.11.092

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ER -

Design and synthesis of an inositol phosphate analog based on computational docking studies

Abstract

Keywords

ASJC Scopus subject areas

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